He’s crazy, calculating and somehow capricious all at the same time. A playground bully who’ll wilt at the first sign of resistance. Or perhaps he just wants us to think he is, and he’s really a master strategist, a latter-day Metternich moving countries and armies around the chessboard of Eastern Europe with a steely determination and an autocrat’s free hand.

From the moment he became president of Russia in a surprise handover from the ailing Boris Yeltsin on New Year’s Eve at the turn of the new millennium, Putin has by turns confused, infuriated, outwitted and just plain befuddled the West. And never more so than in recent days, as Russia has invaded neighboring Ukraine and taken over the Crimean peninsula in the prelude to what could be a full-scale annexation of the territory on the Black Sea, the first time such a maneuver has been pulled in Europe since the blood-soaked end of World War II.

Immediately, however, this much became clear: Putin had shocked everyone by his lightning-fast takeover, and with his small inner circle, KGB officer’s penchant for secrecy and near-complete power, managing the crisis would come down to what we make of Russia’s pugnacious president. Which is why we are once again finding our geopolitics laced with psychoanalysis: This is a crisis whose resolution depends very much on one man.

And, it must be said, when it comes to understanding Vladimir Putin, Washington’s been getting him wrong as often as right for more than a decade now.

***

Not long after I arrived in Moscow at the beginning of 2001 as a correspondent for the Washington Post, I attended the very first presidential interview Putin gave to the American press, a small roundtable at the Kremlin after his first summit meeting with President George W. Bush (the one where Bush looked in his soul). Putin kept us waiting for several hours, then proceeded to impress by reeling off facts and figures from his briefing book; he wasn’t friendly, but he maintained a brisk professionalism until we got about two-thirds of the way around the table. The question of the war in the Russian breakaway republic of Chechnya still hadn’t come up, and I felt obliged to ask about the brutal mayhem and rampant human rights violations in the conflict that had launched Putin on his unlikely path to the presidency the year before. His demeanor quickly changed, and while he didn’t curse or vow to “rub them out in the outhouse” as he had done previously when asked about the Chechen rebels, it was as if an entirely different person was speaking. The modern technocrat of a few minutes earlier vanished, replaced by the threatening tough guy.

But at the time Washington saw mostly the reforming technocrat, a misreading of the man the White House calls VVP—Vladimir Vladimirovich Putin—that would persist in various forms for years. While Vice President Dick Cheney immediately took a strong view of Putin—“KGB, KGB, KGB,” he told one visitor who asked what to make of the onetime Soviet spy—that was not the prevailing analysis in the Bush National Security Council, which forcefully pushed the view of Putin as a liberal economic modernizer out to undo the damage of Russia’s chaotic 1990s. This was when top U.S. officials believed, or at least wanted to, that Putin was there to create a new capitalist Russia, which required ignoring or minimizing that other Putin, the one who ruled with a small cadre of fellow KGB veterans, spoke in messianic terms of Russia’s greatness and fervently—and publicly—expressed the view that democracy was an insidious foreign transplant unsuited for Russian soil. “We still had too many illusions that Putin had been chosen by Yeltsin and was fundamentally an extension of Yeltsin,” recalled one senior U.S. official who dealt with Russia in this period. “We were wrong.”

But already some U.S. diplomats on the ground took a different view, and once Putin began dismantling democratic institutions, cracking down on the media and, eventually, jailing Russia’s richest man for defying him, a sense of Putin as “one cold dude,” as Bush privately told British Prime Minister Tony Blair, became established wisdom. Internal battles still raged for years, though, over what to do about him. When Putin publicly bemoaned the 1991 breakup of the Soviet Union as “the greatest geopolitical catastrophe of the century,” some analysts insisted we should take him seriously, that Putin really meant to restore what he could of the Russian empire; others saw it as mere rhetoric from a calculating realist with whom America could do business.

“There were all kinds of misreadings,” recalled Fiona Hill, who would serve as the top intelligence analyst for Russia at the National Intelligence Council under Bush and later co-wrote the book Mr. Putin: Operative in the Kremlin. “A lot of wishful thinking that Russia has changed.”

By 2008, Bush and Putin were barely on speaking terms in the wake of Russia’s invasion of its tiny neighbor Georgia. But as he won the presidency later that year, Barack Obama again adopted the pragmatist’s view and looked for ways to engage Russia. His “reset” benefited as well from Putin’s temporary hiatus from the Kremlin; unwilling to change the constitution to allow himself to rule for life, he simply traded places with Prime Minister Dmitry Medvedev for a few years, allowing Obama a more congenial if unempowered interlocutor. When Georgian President Mikheil Saakashvili warned a visiting top U.S. official that “he expected Russia to follow its 2008 invasion of Georgia with intervention in Crimea,” as the secret State Department cable recounting the meeting drily noted, no one really took it seriously, and indeed we only know about Saakashvili’s prescient analysis because it was made public with the vast trove of WikiLeaks documents.